


A Stroke of Luck

by LesbianNerd



Category: Pocket Monsters | Pokemon (Main Video Game Series), Pocket Monsters | Pokemon - All Media Types, Pocket Monsters: Sword & Shield | Pokemon Sword & Shield Versions
Genre: Begging, Canon/OC - Freeform, Come Swallowing, Cuddling & Snuggling, Cunnilingus, Degradation, Dominatrix, F/F, Face-Sitting, Forehead Kisses, French Kissing, Groping, Kissing, Lesbian Sex, Light Dom/sub, OC/Canon Relationship, Obedience, Original Character(s), Pokemon Fanfiction, Post-Coital Cuddling, Self-Insert, Teasing, Vaginal Fingering, Verbal Humiliation, this is shameless self insert porn
Language: English
Status: Completed
Published: 2020-01-13
Updated: 2020-01-13
Packaged: 2021-02-27 08:26:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,252
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22233997
Author URL: https://archiveofourown.org/users/LesbianNerd/pseuds/LesbianNerd
Summary: Emi, a woman who does field research, has had her eyes on ex-Macro Cosmos member, Oleana, ever since she began doing research in the Galar Mines. As luck would have it, Oleana notices this newfound attention, and invites Emi over to her home. Emi could have never guessed what Oleana had in store for her.
Relationships: Canon X OC, Oleana/Original Character
Comments: 1
Kudos: 22





	A Stroke of Luck

**Author's Note:**

> Hi! This is my first time writing any kind of porn in a while. Honestly, I only wrote this because I have a pretty big crush on Oleana. I made a character so I could do a self insert ship, and this inspired me to write a fan-fiction. No harm in that, right? Regardless, I hope you enjoy! I would love to go back and edit it some more until I was completely happy with it, but I wanted to just get it out there so it could be read.

Emi, a Pokémon researcher, was busy at work in the Galar Mines. She had gone there in order to study some of the species native to the area, primarily Drilbur: she had been there a couple hours scouting out for one but had no luck in finding any. Feeling a bit discouraged, she laid right up against the rock she was hiding behind and decided to take a quick snack break with her partner Pokémon, Swirlix.

As she reached into her bag to grab her buddy its favorite Wiki Berries, she heard a voice. Someone had found her sitting behind that rock. Emi looked up to find ex-Macro Cosmos secretary, Oleana, towering over her.

"Hey," Oleana said. "I see you're hard at work."

Oh shit.

Emi's mind filled with panic, as, well, at points during her research, she had seen Oleana working and stopped her research to just… admire her. Oleana's beauty was incomparable, and over her trips to the Galar Mines, Emi developed a crush on this woman, but she did not dare speak of it. Plus, even if she did have the guts to say something, she knew it wouldn't go anywhere. She had a feeling Oleana only had strong emotions to her prior boss, Chairman Rose, as she felt it was part of the reason she began volunteer work after her arrest. 

In the midst of her panic, Emi spaced out and was only brought back by the sharp, yet calm tone of Oleana's voice.

"Hey, snap out of it."

Emi blinked her eyes and was brought back. She placed her palm against the rock and pushed herself up onto her feet while her Swirlix happily munched away at its berries.

"You enjoy yourself, Swirlix," the researcher said, "We'll get back to work soon." She then brought her attention back to Oleana. 

Wow… she was even more stunning up close. Though, she was a bit intimidating, too. There was some kind of aura around her that scared Emi, but she spoke.

"Yes, ma'am. I'm a Pokémon researcher from Ballonlea. I've been studying the Pokémon of the mines for a few weeks… What brings you here?" 

Oleana's stern face did not change. "Volunteer work. I used to work for Macro Cosmos, and after I've seen the Chairman's methods, I'm trying to turn a new leaf."

"Yeah, you and Rose were all over the news after the incident with Eternatus…"

For a brief moment, it seems as if Oleana frowned, but she tried to hold it back. "Indeed… He only cared about himself, really. I still appreciate him for helping me out, but… Nevermind that.” Oleana crossed her arms. "You're a new face here. I've seen you quote a bit and thought I'd introduce myself. After all, you seemed to be quite curious about me…"

Oleana smirked, just slightly.

 _Oh no,_ Emi thought. There's no way she caught on to her occasional peeking. Well, maybe it wasn't so occasional.

Emi scratched the back of her ear, hoping Oleana wouldn't notice her face start to flush. "Oh, uh, what do you mean by that?"

"Nevermind that". Oleana reached into her cost pocket and pulled out a piece of card stock, handing it to Emi. "This is my address in Wyndon. I'm trying to meet more people. Come over sometime if you want.”

Emi accepted the slip, and shoved it into her jean pocket. "Uhm, sure. Thank you. Mind if I come over… tonight?"

God, that seemed hasty. Yet, Oleana nodded gently.

"Yes, you may. Be there by 9pm. I'll prep you a surprise. Oleana turned to walk away, but look back and smiled genuinely. "See you later.”

Did… did that really just happen? There is no way that just happened. Emi couldn't deny that it happened, of course, she was just… stunned. Maybe she was just looking for some more friends? Who knows. All Emi knee was that she was going to Oleana's home later, and that she needed the next few hours to fly by. She crouched down and got back to her research, not knowing what was in store for her.

\-------

Emi had no success that day in research progress, but it didn't matter to her. She was going to make a new acquaintance, and said acquaintance was her newfound crush. At the very least, she was hopefully going to make a new friend, which was of benefit to both women.

After touching up at home and switching into a fresh, casual outfit, she made her way to Wyndon through the Corviknight Taxi service.

9PM, on the dot. She had located the correct address, or at least she thought she had, and gave the door a gentle, timid knock. She had to admit, she was quite nervous. She hadn't really been over to someone else's home in ages, and she did not know Oleana's intentions. For all she knew, this could be some elaborate trap. Before anxiety could overrun her thoughts, the door quietly opened and she was greeted by Oleana, in her usual attire.

"You made it," Oleana said. "Come in."

Oleana held the door open for Emi, who was trying her best to steel her nerves. Her house seemed pretty basic in decor, yet strangely beautiful. Everything was neatly arranged and looked well kept. 

Oleana invited Emi over to the dinner table. She had prepped some omelets for them. Over dinner, Oleana discussed some of her hardships related to the Chairman and how she was looking to reconnect with people after that incident, so she was thankful that Emi was willing to accept the invite. She seems to be holding back some sort of anger, but Oleana did her best and keeping those feelings from spilling out. The way she spoke to Emi calmed any kind of worry she had prior to their meetup; well, all but her nerves related to her attraction. She found herself spacing out a few times due to how much she got into just listening to Oleana's vocals, but was able to move past them. It was a relaxing dinner, and afterward, Emi offered to help clean up, but Oleana refused.

"I like to keep control of the cleaning here," Oleana said. "If you would like to stay longer, you can go hang around in my room. It's down the hall. There's a television in there. I'll meet you when I'm done."

Emi nodded and made her way to the bedroom. Again, everything looked rather simple, yet pleasing to the eye. She went to go find the buttons on the television, but was interrupted when the door closed behind her. 

"Already?" Emi said as she turned around. "You're fast."

"Oh, I decided those could wait. Besides," Oleana said, approaching Emi and hanging her arms over Emi's shoulders, "I have some much more interesting ideas, if you're up to it."

 _Where did that come from?_ Confused, Emi asked, "What's this all about?"

"I know you're into me. It's obvious," Oleana said with a seductive smirk. "Come on, you don't have to keep that secret."

So, she did know. Why was she so… intimate all of a sudden? It threw Emi off a little… but she wasn't going to deny the affection she was receiving. She didn't say anything. She simply made a small nod. Oh god, this was hot. Emi felt like she would like where this was going, even if this shift in attitude confused her.

"Can I kiss you?" Oleana asked' stroking Emi's hair with one hand.

Emi's rational brain would have said no, as she had _just_ met this woman today. But Emi was not thinking rationally. She could not believe this was happening to her. Her desire for affection from Oleana took over and she told Oleana yes.

In one instant, Oleana's gripped Emi's shoulders and her lips locked with Emi's. Emi's eyes shot open for a second, but then closed as she accepted the kiss. Emi's mouth was forced open by Oleana's tongue, and she allowed it to happen. Oleana wanted to make that kiss as passionate as she could.

As their lips came apart, Emi took a small breath before Oleana went back in again. Damn, was this girl affectionate. Oleana began to step forward. Emi followed her step as she was backed up until her heel hit the bed. Still interlocked, Oleana pushed forward, causing Emi to talk backwards onto her bed. She moved her hands onto the mattress on each side of Emi, and Emi instinctively wrapped her arms around Oleana's back.

This was not what Emi imagined what would happen tonight, but damn, was she enjoying it. 

Oleana finally ceased her kiss and Emi gasped for air. Oleana ran her finger down the middle of Emi's body, slowly as she looked Emi directly in the eyes.

"I knew you would like that," Oleana said. Her voice was almost hypnotic, in a way, and Emi was falling for her spell, as a strange feeling of arousal started to grow stronger. She hoped this was not the end of it, and lucky for her, Oleana wanted more of her.

Oleana's finger stopped at the rim of Emi's pants. Teasingly, she said "I bet you would like even more of me, hmm?"

"Yes, please…" Emi panted. This was it. She couldn't go back. She did not care that this was their only meeting and it was already becoming erotic- she _desparately_ wanted this.

Oleana, happy to oblige, reached her hand on Emi's jean zipper, pulling it down as Emi grew even more red in the face.

"Oh, it's too easy to make you blush," Oleana said, her voice oh-so enticing. She undid Emi's buttons as well, until she could see the slightest glimpse of Emi's panties.

Oleana slipped her hand though Emi's panties. Emi let out a needy sound, almost like a whimper, as Oleana lightly touched the lip of her pussy.

"You're already this wet? Aren't you a dirty little slut, huh?" Oleana said, a bit more stern. Oh yes, this is exactly what Emi liked. She didn't care what nasty things were said to her: domination of any kind turned her on, and it seemed like Oleana was just the type to want to be dominant.

Oleana stood up, getting up off of Typh. After licking Emi's juices off of her finger, she commanded Emi. "Get yourself fully on the bed. Now."

Emi, eager to please, pivoted until her whole body was on the bed. She loved how demanding Oleana seems to be.

"Good girl. Now, sit up."

Just like last time, Emi obeyed.

Oleana moved so she was in front of Emi again and put her palms down on the front of Emi's breasts. 

"I'm going to reward you real well if you behave, and I know a slut like you is going to _love_ it."

Her words continued to make Emi hornier and hornier, and more desperate for her to continue. She _needed_ this and she needed it _now._

"Let me get these off for you," Oleana said as she began to tug at Emi's shirt. She reached for the bottom for her shirt and worked it off her body, revealing her basic bra that she wore underneath. She then moved down to her pants, slowly pulling them off of her legs until she was only left in her underwear.

"Well, aren't you cute," Oleana said alluringly, admiring Emi's body for a moment. 

Emi felt a little self conscious about her body, but Oleana loved it. She put her hands on her stomach, and teasing again, stroked Emi's body gently until she got a hold of her bra straps. She tugged the straps upward and then let go, letting them slap her shoulders. Emi grunted quietly in pain from the impact.

Oleana reached back and unhooked her bra, taking a hold of the straps again.

"You're behaving so well… This won't go unnoticed, you know."

Oleana pulled the strapped over Emi's arms, grabbed her bra and chucked it to the floor, revealing her ample breasts. Simply getting to see Emi's body near nude was enough to turn on Oleana, but her pure arousal would come from being able to dominate and satisfy her.

Emi finally spoke again. "You can touch them, if you want…"

She really wanted her breasts touched. She was hoping this would be a way to entice Oleana to take action, and it was, and she reached down and softly squeezed one breast.

"You don't need to invite me to do so," Oleana said. She pushed Emi back down, making sure her head hit the pillows as she now grouped both of Emi's boobs, fondling them in a slow rhythm. "I'm the one in charge here."

Oleana continued to fondle her breasts, occasionally gripping them, causing Emi to moan very quietly. She couldn't help herself, and she felt like before long, she will lose any sort of control of when she responds to Oleana's affection.

"Oh, you like this?" Oleana asked. Emi nodded, keeping eye contact with Oleana.

"Yes, please… keep going."

Oleana gave her breasts a few more firm squeezes before stopping. Emi was a bit disappointed when she stopped, but Oleana made sure that disappointment would not last. Oleana got up off of Emi and on her knees, still on the bed.

"Stay down," Oleana commanded, pulling the ends of her white jacket as far out as she could before swiftly removing it. Her red shirt quickly followed, leaving Oleana in a fancy piece of lingerie. She then stood up and removed her bottoms with alluring movements: Emi was fully enticed by the way she teaser her. Oleana's panties were just as detailed and lacey as her bra.

Crawling back onto the bed, she slowly got back over Emi, and with her breasts in Emi's face to give her a good look at her cleavage, she cupped them, swaying her chest ever so slightly, back and forth. She caught Emi staring right at them.

"You want to see these, _don't you?_ "

"Yes…" Emi responded timidly. She had to be honest here.

"I knew it. I want you to _beg._ _Beg_ for for them, come on."

 _She was too damn good at this._ Oleana had Emi under her spell at this point, and she was going to listen to whatever she demanded, almost out of instinct.

"Let me see your breasts, Miss Oleana…"

"Beg more, bitch."

"Please let me see your breasts! Please! I've never seen breasts in person and I… I'm desperate!"

"Damn right, you're desperate!"

"Please!" Emi exclaimed, her voice rising. "You're beautiful, Miss Oleana. I need you. I need more of you!"

"Very good." Oleana said softly before grasping onto her bra clasp. "Look, but don't touch.” With that, she tore her bra right of in one motion, her breasts bouncing slightly as they were freed.

Emi wasn't lying: this was her first time seeing anyone this nude in person, and of course, her first time receiving any kind of this affection. It felt so damn nice being rewarded simply for following command. They were just breasts, yes, but to Emi, they were absolutely stunning.

After another quick tease, Oleana got up, straddling Emi. She, too, was excited for what was to come. She got some kind of thrill from teasing Emi, and found it cute how desperate she behaved in order for Oleana to continue on, and it felt rewarding to finally have someone she could be this intimate with, even if they had only just met. She didn't care, and apparently so didn't Emi. 

While she received satisfaction simply by satisfying a partner, Oleana was not going to leave this without receiving pleasure herself, though.

"You're so close to your reward, hon," Oleana said while clasping the band of Emi's panties. She was so close, yet _oh so far_. Emi just wanted to be touched, but it was not going to come that easy.

Oleana grabbed her own panties and, while still straddling Emi, proceeded to finally remove those. "If you want your reward, you're going to have to do a little something for me.”

Oleana was fully exposed, and Emi could not stop admiring her. She was honestly jealous of her figure, but was of course aroused too. She couldn't comprehend how a woman could be _this_ damn beautiful. 

Emi was so lost in her thoughts that she did not realize that Oleana was nearly right above her face. She knew exactly where this was going.

"Pleasure me," Oleana demanded.

"Wait, I haven't done this befo-"

"No objections, okay? I don't care what your experience is, you're going to pleasure me!" The harsh tone she said that was intimidating yet oddly sexy. 

Before Emi could say another world, Oleana planted herself down, her pussy right over Emi's mouth.

Emi got right to work, using her tongue to lap her partner up, and honestly, she did not know exactly what she was doing. Yet, she could tell Oleana was enjoying it, as she began to quietly moan. Even those were enough to drive Emi crazy. This woman was just so damn hot.

"Mmm… you can do better than that," Oleana claimed. She began to grind her hips against Emi's mouth in order to wring as much pleasure as she could out of it.

Oleana's moans got a bit louder, yet the tone remained in a low growl, encouraging Emi to try even harder. Her mind was only on two things: Satisfying Oleana's demands and performing well for a better reward.

Emi felt she may run out of breath, but luckily Oleana bucked her hips up for a moment before planting herself right down again. She shifted her hips back a bit so that Emi could reach her clit. Emi gripped the bed sheets go keep her body stable as she worked on her clit specifically, which was nearly enough to push Oleana over the edge.

"You really know your stuff, you dirty little whore!"

Those words made Emi determined. She lifted her head off the pillow to get as much force as she could, and while swirling her tongue on Oleana's pussy, could feel her cum as she let out a long, low moan.

"Ha…" Oleana sighed, slightly out of breath. "Thought you said you hadn't done this before." She lifted her body up so Emi could speak.

"I haven't, but that was almost ins-"

"Well, you did well.” Oleana brought her hips back down. She wasn't done with her demands. "Lick me clean.”

Eagerly, Emi obeyed, lapping up Oleana's cum. She did not particularly like the taste, but Oleana's word was final. When she stopped, Oleana got completely off of her need and stood by her side, watching Emi like a hawk.

"Swallow it.”

Wincing, Emi clenched her eyes and face, and swallowed. She looked up at Oleana, who seemed pleased with Emi.

Oleana swayed her body in an alluring fashion as she made her way back to the other side of the bed. Emi watched every step, and as she climbed back over Emi, Emi's breath became shallow and quick. She was ready.

"You've been a _very_ good girl," Oleana said, her tone as enticing as ever. "I think it's about time I give you what you've been waiting for.”

Oleana ran her finger tip in circles over the top of Emi's panties. God damn it, she knew how to keep her in near permanent anticipation. This would make it all the more satisfying, though.

Oleana leaned up for a moment in order to clasp Emi's underwear, pulling them down. Slowly. Emi observed every single second of it, as her body became fully revealed. She had Emi shake the panties off of her ankles. Almost out of nerves, Emi kept her legs clamped shut, but Oleana was not having it. She stayed in position where she could see nearly Emi's whole body and glared at her.

"Spread your legs open," she demanded.

Emi was a bit hesitant, and did not open up at first, promptly Oleana to speak again.

"Open them up! My bitch wants her reward, doesn't she?" She seemed a bit angry, but of course, it was all part of the bedroom play.

Emi spread her legs apart, almost instinctively, just enough for Oleana to get a good view of her pussy. Only looking for a second, she climbed over Emi one last time, reaching one hand backwards until she could feel Emi's pussy lips.

"Very good," Oleana said, whispering. "You better enjoy this.” Oleana put one finger over Emi's clit, gently pressing. "I want to hear the sound of you writhing in pleasure. Don't hold back on me.”

"Yes, ma'am…"

With no hesitation, Oleana began stroking Emi's clit, and it already felt _oh so_ good.

"Ah… Oleana… Keep going, please!"

Oleana smirked. "With pleasure.”

Oleana stopped touching her clit and jammed two fingers into Emi's pussy with zero hesitation. The sudden impact made Emi cry loudly, and Oleana interrupted it with a kiss. Swiftly, she pulled her fingers out and roughly jabbed them in again.

"Mmmph… mppph!" Oleana's lips prevented Emi from being noisy, but she was sure crying out in absolute bliss. Oleana ceased the kiss and observed Emi, her eyes shut and her jaw open as she panted. 

Oleana focused on pure speed, not slowing down her rhythm for a second. She herself sighed as she listened to Emi moaning _loudly_ , the sound echoing against the walls. With her free hand, she grabbed onto Emi's breast, but continued to focus on fingering. 

"You're _such_ a naughty little _bitch_ ," Oleana taunted as she took her fingers out, knowing it would leave Emi aggravated.

"Why'd you stop?"

"I need to know how much you want me and how much of a dirty whore you are…"

"I want you to be the first person to make me cum, Oleana! I need you to!"

"Why me?"

Emi felt the sense of pleasure fading, and was worried she wouldn't get that desired orgasm if she didn't begin soon. She begged like her life was dependent on it.

"You're so hot Oleana… you're so good at this. I want to to aggressively finger me until my legs buckle, I want you to have absolute control over me. Please!"

"You're so dirty. I _like_ it.” Oleana put two fingers over Emi's clit again, and pushed hard as she began to run.

Breathless, Emi moaned out, "Yes! Mmmn! Oleana, I'm… mnn!" She couldn't find the words for it, as her sounds of pleasure continued to interrupt her. She was nearly there. 

Oleana stopped for one brief moment, only to readjust herself so that both of her arms could reach. As she used one hand to rub her clit, she put three fingers together and rapidly stroked the inside of her pussy. Her dexterity skills to be able to do this was outstanding.

This was enough to bring Emi to climax. With one last ferocious moan, the most blissful sense of pleasure overcame her as she was brought to a powerful orgasm, much more powerful than anything she could achieve on her own. Her toes and fingers curled into the mattress as she came, with Oleana slowing down, yet not stopping to wring out her orgasm for as long as she could. 

Oleana withdrew her fingers, now soaked. Emi's cum trickled down her body and drilled onto the bed sheets. She walked over to her dresser to grab a box of tissues, wiping her own fingers off before using one to help clean up Emi.

Emi was in absolute disbelief. Smiling, she ruminated about what had just transpired, and honestly thought that this might have been some crazy dream. All of that happened so quickly… so conveniently. She snapped out of her thoughts when Oleana brought a blanket over and covered Emi up with it before laying next to her.

Emi wanted to inquire about this.

"So…" Emi said, "What was that all about?"

Oleana shifted her eyes away for a second, hugging onto part of the blanket, before looking over at Emi. "Honestly, I'm not sure myself, but I caught on that you were admiring me in a way, and I definitely could have used the company.” In a moment of her own self doubt, she asked, "You did like that, right?"

"Of course! I'm just… surprised. You're so stunning, such a big name in Galar, and I'm just… some Pokémon researcher. I never thought you'd wanna… well, get with someone like me."

Oleana moved closer, swapping to her side and wrapping her arms around Emi.

"People may not know your name, but that doesn't make you any less cute to me. I admire your hard work. This was a good opportunity for the both of us."

Wow. Oleana, _the_ Oleana, was singing such high praise about her. It was certainly an odd shift from her prior dominatrix behavior in bed. She was truly a tender woman inside.

Emi smiled.

"Yeah… I guess it was. Thank you."

"You're welcome," Oleana replied, kissing Emi on the forehead. "If you'd like, this doesn't have to be the end for us. What do you think?"

"I… think I'd like that a lot."

With those words, Oleana stretched over to shut her table lamp off, and the two fell asleep together, entangled in each other's arms. The did not care that this was a weird start to a relationship, as it brought on a wonderful connection that the both of them needed in their lives.

"Let's do this again sometime.”


End file.
